Para-phenylenediamine derivatives comprising a cyclic diaza group substituted with a cationic radical, and use of these derivatives for dyeing keratin fibers

ABSTRACT

The disclosure relates to novel para-phenylenediamine derivatives containing a cyclic diaza group, substituted with a cationic radical, as well as to the dye compositions comprising them, and to the method of dyeing keratin fibers using these compositions. 
     The present invention may make it possible to obtain a chromatic, strong, relatively unselective and fast coloration on keratin fibers.

This application claims benefit of U.S. Provisional Application No.60/467,123, filed May 2, 2003.

The present disclosure relates to novel para-phenylenediaminederivatives comprising a cyclic diaza group substituted with a cationicradical, to the dye compositions comprising at least onepara-phenylenediamine as disclosed herein, and to a process for dyeingkeratin fibers using these dye compositions.

It is known practice to dye keratin fibers, for instance, human hair,with dye compositions containing oxidation dye precursors, such asortho- or para-phenylenediamines, ortho- or para-aminophenols,heterocyclic compounds such as diaminopyrazole derivatives,pyrazolo[1,5-a]pyrimidine derivatives, pyrimidine derivatives, pyridinederivatives, 5,6-dihydroxyindole derivatives and 5,6-dihydroxyindolinederivatives, which may also be referred to as oxidation bases. Oxidationdye precursors, or oxidation bases, are colorless or weakly coloredcompounds that, when combined with oxidizing products, can give rise tocolored compounds and dyes by a process of oxidative condensation.

It is also known that the shades obtained with these oxidation bases maybe varied by combining them with couplers or coloration modifiers, thelatter being chosen from, for example, aromatic meta-diamines,meta-aminophenols, meta-hydroxyphenols and certain heterocycliccompounds such as, for example, pyrazolo[1,5-b]-1,2,4-triazolederivatives, pyrazolo[3,2-c]-1,2,4-triazole derivatives,pyrazolo[1,5-a]pyrimidine derivatives, pyridine derivatives,pyrazol-5-one derivatives, indoline derivatives and indole derivatives.

The variety of molecules that may be used as oxidation bases andcouplers allows a wide range of colors to be obtained.

The “permanent” coloration obtained with these oxidation dyes should,moreover, satisfy a certain number of requirements. For instance, itshould have no toxicological drawbacks, allow shades to be obtained inthe desired intensity, and show good resistance to external agents suchas light, bad weather, washing, permanent-waving, perspiration andrubbing.

The dyes should also allow white hairs to be covered. Additionally, thedyes should be as unselective as possible, i.e., they must produce thesmallest possible color differences along the same length of keratinfiber, which may be differently sensitized (i.e., damaged) between itsend and its root. They should also show good chemical stability in theformulations, and have a good toxicological profile.

In the field of hair dyeing, para-phenylenediamine andpara-tolylenediamine are oxidation bases that are widely used. They givevaried shades with oxidation couplers.

However, there is a need in the art for novel oxidation bases that havea better toxicological profile than para-phenylenediamine andpara-tolylenediamine, while at the same time giving the hair excellentproperties in terms of color intensity, variety of shades, coloruniformity and fastness with respect to external agents.

It is already known to use para-phenylenediamine derivatives substitutedwith a pyrrolidine group as oxidation bases for dyeing keratin fibers asreplacements for para-phenylene-diamine. For example, U.S. Pat. No.5,851,237 describes the use of 1-(4-aminophenyl)pyrrolidine derivativesoptionally substituted on the benzene nucleus. U.S. Pat. No. 5,993,491proposes the use of N-(4-aminophenyl)-2-hydroxymethylpyrrolidinederivatives optionally substituted on the benzene nucleus and on thepyrrolidine heterocycle in position 4 with a hydroxyl radical.

Patent Application JP 11-158,048 teaches compositions containing atleast one compound chosen from para-phenylene-diamine derivativesoptionally substituted on the benzene nucleus, and one of the nitrogenatoms of which is included in a 5- to 7-membered carbon ring.

Publication DE 197 07 545 describes the use of para-phenylenediaminecompounds in which one of the amino groups forms a diazacycloheptane,for dyeing keratin fibers.

However, the compounds described in the above mentioned references donot make it possible to give the hair a coloration that is equivalent inquality to that obtained with para-phenylenediamine or withpara-tolylenediamine due to the lack of intensity and uniformity ofcolor.

The present inventors, therefore, have developed novel dye compositionsthat may not have the drawbacks of the oxidation bases of the prior art.For example, the present inventors provide herein novel oxidation basesthat simultaneously have a good toxicological profile and propertiessuch that the dye compositions comprising them do not degrade keratinfibers, while at the same time being capable of generating colorationsin varied shades that are, for example, strong, unselective and fast.

Thus, disclosed herein is a compound of formula (I), wherein thecompound is a para-phenylenediamine derivative substituted with a cyclicdiaza group, and addition salts thereof:

wherein

-   -   a ranges from 0 to 4, it being understood that when a is greater        than or equal to 2, then the radicals R₁ may be identical or        different,    -   b ranges from 0 to 4, it being understood that when b is greater        than or equal to 2, then the radicals R₄ may be identical or        different,    -   c is equal to 0 or 1,    -   R₁ may be chosen from halogen atoms; C₁–C₈ aliphatic and        alicyclic, saturated and unsaturated, hydrocarbon-based chains        wherein at least one carbon atom may be replaced with at least        one entity chosen from oxygen, nitrogen, silicon and sulphur        atoms and an SO₂ group; and an onium radical Z; with the proviso        that the radical R₁ does not comprise a peroxide bond or diazo,        nitro or nitroso radicals,    -   R₂ comprises an onium radical Z, wherein an onium radical is a        nitrogen-based quaternary radical,    -   R₃ may be chosen from        -   an alkyl radical;        -   an alkenyl radical;        -   an alkynyl radical;        -   a hydroxyl radical;        -   a hydroxyalkyl radical;        -   an alkoxy radical;        -   an alkoxyalkyl radical;        -   an alkylcarbonyl radical;        -   a hydroxyalkoxyalkyl radical;        -   an amino radical;        -   a monoalkylamino radical;        -   a dialkylamino radical;        -   an aminoalkyl radical;        -   an aminoalkyl radical wherein the amine is monosubstituted            or disubstituted with at least one radical chosen from            alkyl, acetyl and hydroxyalkyl radicals;        -   a hydroxyl radical;        -   an aminoalkyl radical;        -   a carboxyl radical;        -   a carboxyalkyl radical;        -   a carbamoyl radical;        -   a carbamoylalkyl radical;        -   an alkoxycarbonyl radical;        -   a monoalkylaminocarbonyl radical;        -   a dialkylaminocarbonyl radical;        -   a monoalkylaminocarbonylalkyl radical; and        -   a dialkylaminocarbonylalkyl radical;    -   R₄ may be chosen from        -   an alkyl radical;        -   an alkenyl radical;        -   an alkynyl radical;        -   a hydroxyalkyl radical;        -   an alkoxyalkyl radical;        -   an alkylcarbonyl radical;        -   a hydroxyalkoxyalkyl radical;        -   an aminoalkyl radical;        -   an aminoalkyl radical wherein the amine is monosubstituted            or disubstituted with at least one radical chosen from            alkyl, acetyl and hydroxyalkyl radicals;        -   a hydroxyl radical;        -   a aminoalkyl radical;        -   a carboxyl radical;        -   a carboxyalkyl radical;        -   a carbamoyl radical;        -   a carbamoylalkyl radical;        -   an alkoxycarbonyl radical;        -   a monoalkylaminocarbonyl radical;        -   a dialkylaminocarbonyl radical;        -   a monoalkylaminocarbonylalkyl radical; and        -   a dialkylaminocarbonylalkyl radical.

Also disclosed herein are the nitro derivatives of formula (I′) includedin the synthesis of the derivatives of formula (I) as presentlydisclosed.

Further disclosed herein is a dye composition comprising at least onepara-phenylenediamine compound of formula (I) as an oxidation base.

Yet another aspect of the present disclosure is the use of theaforementioned composition for dyeing keratin fibers and the process fordyeing keratin fibers, for instance human keratin fibers such as hair,using the composition of the present disclosure.

The composition of the present disclosure, for example, makes itpossible to obtain a chromatic, powerful, unselective and fastcoloration of keratin fibers.

In the context of the present disclosure, an aliphatic hydrocarbon-basedchain is a linear or branched chain that may contain unsaturations ofthe alkene or alkyne type. An alicyclic hydrocarbon-based chain is asaturated or unsaturated, branched chain not containing an aromaticcyclic structure.

The term “onium” means a nitrogen-based quaternary radical.

The compounds of formula (I) are para-phenylenediamines wherein oneamine is included in a ring of 1,4-diazacycloheptane type, this ringalso being referred to in the literature as 1,4-diazepane, or whereinone amine is included in a ring of 1,4-diazacyclohexane type, which isalso referred to in the literature as 1,4-piperazine.

In formula (I) above, R₁ may be chosen from C₁–C₄ alkyl radicals, C₁–C₄alkoxyalkyl radicals, C₁–C₄ hydroxyalkyl radicals, C₁–C₄ aminoalkylradicals, C₁–C₄ alkoxy radicals, C₁–C₄ hydroxyalkoxy radicals, and C₁–C₄carboxyalkyl radicals.

By way of non-limiting example, R₁ may be chosen from a chlorine atom,and from methyl, ethyl, isopropyl, vinyl, allyl, methoxymethyl,1-hydroxyethyl, 1-carboxymethyl, 1-aminomethyl, 2-carboxyethyl,2-hydroxyethyl, 3-hydroxypropyl, 1,2-dihydroxyethyl,1-hydroxy-2-aminoethyl, 1-amino-2-hydroxyethyl, 1,2-diaminoethyl,methoxy, ethoxy, allyloxy and 2-hydroxyethyloxy radicals.

According to one aspect of the present disclosure, R₁ may be chosen fromchlorine, bromine, and from C₁–C₄ alkyl, C₁–C₄ hydroxyalkyl, C₁–C₄aminoalkyl, C₁–C₄ alkoxy and C₁–C₄ hydroxyalkoxy radicals. R₁ may, forinstance, be chosen from methyl, hydroxymethyl, 2-hydroxyethyl,1,2-dihydroxyethyl, methoxy, isopropyloxy and 2-hydroxyethoxy radicals.

In one embodiment, a may be equal to 0 or 1, for example, a may be 0.

In another embodiment, R₂ comprises an onium radical Z corresponding toformula (II)

wherein

-   D is a linker arm chosen from a covalent bond and from linear and    branched C₁–C₁₄ alkylene chains which may comprise at least one    hetero atom chosen from oxygen, sulphur and nitrogen, and which may    be substituted with at least one radical chosen from hydroxyl and    amino radicals, and which may further comprise at least one carbonyl    radical;-   R₈, R₅ and R₆, which may be identical or different, may each be    chosen from C₁–C₁₅ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals;    C₂–C₆ polyhydroxyalkyl radicals; (C₁–C₆)alkoxy(C₁–C₆)alkyl radicals;    aryl radicals; benzyl radicals; C₁–C₆ carbamoylalkyl radicals;    tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆ aminoalkyl    radicals; C₁–C₆ aminoalkyl radicals wherein the amine is mono- or    disubstituted with a radical chosen from C₁–C₄ alkyl,    (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals;    and quaternary ammonium radicals;-   R₈, R₅ and R₆ together, in pairs, may form, with the nitrogen atom    to which they are attached, a saturated 4-, 5-, 6- or 7-membered    carbon-based ring optionally comprising at least one hetero atom,    wherein the ring may possibly be substituted with a radical chosen    from a hydroxyl radical, C₁–C₆ alkyl radicals, C₁–C₆    monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆    alkoxy radicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals,    carbamoyl radicals, carboxyl radicals, (C₁–C₆)alkylcarbonyl    radicals, amino radicals, and amino radicals mono- or disubstituted    with at least one radical chosen from (C₁–C₆)alkyl,    (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals;-   R₇ may be chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl    radicals; C₂–C₆ polyhydroxyalkyl radicals; aryl radicals; benzyl    radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals    wherein the amine is mono- or disubstituted with at least one    radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl    and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carboxyalkyl radicals;    C₁–C₆ carbamoylalkyl radicals; C₁–C₆ trifluoroalkyl radicals;    tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆ sulphonamidoalkyl    radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals;    (C₁–C₆)alkylsulphinyl(C₁–C₆)alkyl radicals;    (C₁–C₆)alkylsulphonyl(C₁–C₆)alkyl radicals;    (C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals;    N—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals; and    N—(C₁–C₆)alkylsulphonamido(C₁–C₆)alkyl radicals;    -   x is equal to 0 or 1, provided that        -   when x=0, then the linker arm D is attached to the nitrogen            atom bearing the radicals R₅, R₆ and R₈,        -   when x=1, then two of the radicals R₅, R₆ and R₈ form,            together with the nitrogen atom to which they are attached,            a 4-, 5-, 6- or 7-membered saturated ring and the linker arm            D is linked to a carbon atom of the saturated ring;    -   Y is a counterion.

According to this aspect of the present disclosure, x may be, forexample, equal to 0, and R₅, R₆ and R₈, which may be identical ordifferent, may each be chosen from C₁–C₆ alkyl radicals, C₁–C₄monohydroxyalkyl radicals, C₂–C₄ polyhydroxyalkyl radicals,(C₁–C₆)alkoxy(C₁–C₄)alkyl radicals, C₁–C₆ carbamoylalkyl radicals, andtri(C₁–C₆)-alkylsilane(C₁–C₆)alkyl radicals, or R₈ and R₅ together mayform a ring chosen from azetidine, pyrrolidine, piperidine, piperazineand morpholine, wherein R₆ may be chosen from C₁–C₆ alkyl radicals;C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆aminoalkyl radicals, aminoalkyl radicals mono- or disubstituted with atleast one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl,carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carbamoylalkylradicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals;(C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals;(C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; andN—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals.

According to still another aspect, x is equal to 1, and R₇ may be chosenfrom C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆polyhydroxyalkyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkylradicals wherein the amine is mono- or disubstituted with at least oneradical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and(C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carbamylalkyl radicals;tri(C₁–C₆)-alkylsilane(C₁–C₆)alkyl radicals;(C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals;(C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; andN—(C₁–C₆)alkylcarbamyl(C₁–C₆)alkyl radicals; R₈ and R₅ together form aring chosen from azetidine, pyrrolidine, piperidine, piperazine andmorpholine rings, wherein R₆ may be chosen from C₁–C₆ alkyl radicals;C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆aminoalkyl radicals; C₁–C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with at least one radical chosen from(C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonylradicals; C₁–C₆ carbamoylalkyl radicals;tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals;(C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals;(C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; andN—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals.

By way of a non-limiting example according to this aspect of thedisclosure, R₂ may comprise a trialkylammoniumalkyl radical, wherein thealkyl linking R₂ to the ring may possibly be substituted with at leastone hydroxyl group.

For instance, D may be chosen from a covalent bond and an alkylene chainthat may be substituted and that may comprise a carbonyl group.

According to yet another aspect of the present disclosure, R₂ comprisesan onium radical Z corresponding to formula (III):

wherein

-   -   D is a linker arm chosen from a covalent bond and from linear        and branched C₁–C₁₄ alkylene chains, which may comprise at least        one hetero atom chosen from oxygen, sulphur and nitrogen, and        which may be substituted with at least one radical chosen from        hydroxyl and amino radicals, and which further may comprise at        least one carbonyl radical;    -   the ring members E, G, J and L, which may be identical or        different, may be chosen from carbon, oxygen, sulphur and        nitrogen atoms to form a ring chosen from pyrrole, pyrazole,        imidazole, triazole, oxazole, isoxazole, thiazole and        isothiazole rings,    -   q is an integer ranging from 1 to 4;    -   R, which may be identical or different, may be chosen from a        hydrogen atom, halogen atoms, hydroxyl radicals, C₁–C₆ alkyl        radicals, C₁–C₆ monohydroxyalkyl radicals, C₂–C₆        polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals,        tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoyl radicals,        carboxyl radicals, C₁–C₆ alkylcarbonyl radicals, amino radicals,        amino radicals mono- and disubstituted with at least one radical        chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and        (C₁–C₆)alkylsulphonyl radicals, C₁–C₆ monohydroxyalkyl radicals        C₂–C₆ polyhydroxyalkyl radicals, and quaternary ammonium        radicals;    -   R₇ may be chosen from C₁–C₆ alkyl radicals; C₁–C₆        monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; aryl        radicals; benzyl radicals; C₁–C₆ aminoalkyl radicals, C₁–C₆        aminoalkyl radicals wherein the amine is substituted with a        radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl,        carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carboxyalkyl        radicals; C₁–C₆ carbamoylalkyl radicals; C₁–C₆ trifluoroalkyl        radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆        sulphonamidoalkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl        radicals; (C₁–C₆)alkylsulphinyl(C₁–C₆)alkyl radicals;        (C₁–C₆)alkylsulphonyl(C₁–C₆)alkyl radicals;        (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals;        N—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals;        N—(C₁–C₆)alkylsulphonamido(C₁–C₆)alkyl radicals; and quaternary        ammonium radicals;    -   x is equal to 0 or 1, with the proviso that        -   when x=0, the linker arm D is attached to the nitrogen atom,        -   when x=1, the linker arm D is attached to one of the ring            members E, G, J or L, and    -   Y⁻ is a counterion.

According to this aspect of the disclosure, the ring members E, G, J andL form, for example, a ring chosen from pyrrole, imidazole, pyrazole,oxazole, thiazole and triazole rings. For instance, the ring members E,G, J and L may form an imidazole ring.

When x is equal to 0, D may be, for example, chosen from a covalent bondand an alkylene chain that may be substituted and/or that may comprise acarbonyl function.

According to yet still another aspect of the present disclosure, R₂comprises an onium radical Z corresponding to formula (IV):

wherein:

-   -   D is a linker arm chosen from a covalent bond and from linear        and branched C₁–C₁₄ alkylene chains, which may comprise at least        one hetero atom chosen from oxygen, sulphur and nitrogen atoms,        and which may be substituted with at least one radical chosen        from hydroxyl and amino radicals, and which further may comprise        at least one carbonyl radical;    -   the ring members E, G, J, L and M, which may be identical or        different, may be chosen from carbon, oxygen, sulphur and        nitrogen atoms, and thus form a ring chosen from pyridine,        pyrimidine, pyrazine, triazine and pyridazine rings;    -   m is an integer ranging from 1 to 5;    -   R, which may be identical or different, may be chosen from a        hydrogen atom, halogen atoms, hydroxyl radicals, C₁–C₆ alkyl        radicals, C₁–C₆ monohydroxyalkyl radicals, C₂–C₆        polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals,        tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoyl radicals,        carboxyl radicals, C₁–C₆ alkylcarbonyl radicals, amino radicals,        amino radicals substituted with a radical chosen from        (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and        (C₁–C₆)alkylsulphonyl radicals, C₁–C₆ monohydroxyalkyl radicals,        C₂–C₆ polyhydroxyalkyl radicals, and quaternary ammonium        radicals;    -   R₇ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl        radicals; C₂–C₆ polyhydroxyalkyl radicals; aryl radicals; benzyl        radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals        wherein the amine is mono- and disubstituted with a radical        chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and        (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carboxyalkyl radicals;        C₁–C₆ carbamoylalkyl radicals; C₁–C₆ trifluoroalkyl radicals;        tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆        sulphonamidoalkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl        radicals; (C₁–C₆)alkylsulphinyl(C₁–C₆)alkyl radicals;        (C₁–C₆)alkylsulphonyl(C₁–C₆)alkyl radicals;        (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals;        N—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals;        N—(C₁–C₆)alkylsulphonamido(C₁–C₆)alkyl radicals; and quaternary        ammonium radicals;    -   x is equal to 0 or 1, with the proviso that        -   when x=0, the linker arm D is attached to the nitrogen atom,        -   when x=1, the linker arm D is attached to one of the ring            members E, G, J, L or M, and    -   Y⁻ is a counterion.

In this aspect, the ring members E, G, J, L and M may form, for example,with the nitrogen of the ring, a ring chosen from pyridine andpyrimidine rings.

For further example, when x is equal to 0, then R may be chosen from ahydrogen atom, hydroxyl radicals, C₁–C₆ alkyl radicals, C₁–C₆monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxyradicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoylradicals, C₁–C₆ alkylcarbonyl radicals, amino radicals, amino radicalsmono- and disubstituted with at least one radical chosen from(C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonylradicals; C₁–C₆ monohydroxyalkyl radicals and C₂–C₆ polyhydroxyalkylradicals.

As yet another example, when x is equal to 1, R₇ may be chosen fromC₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆polyhydroxyalkyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkylradicals wherein the amine is mono- or disubstituted with at least oneradical chosen from (C₁–C₆)alkyl radicals, (C₁–C₆)alkylcarbonylradicals, a carbamoyl radical and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆carbamoylalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals;(C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; andN—(C₁–C₆)alkylcarbamyl(C₁–C₆)alkyl radicals; R may be chosen from ahydrogen atom, hydroxyl radicals, C₁–C₆ alkyl radicals, C₁–C₆monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxyradicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoylradicals, C₁–C₆ alkylcarbonyl radicals, amino radicals, amino radicalsmono- and disubstituted with at least one radical chosen from(C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonylradicals.

For instance, R may be chosen from a hydrogen atom and alkyl radicalsthat may be substituted, and R₇ comprises an alkyl radical that may besubstituted.

According to another aspect of the present disclosure, R may be chosenfrom hydrogen; alkyl radicals; alkyl radicals substituted with at leastone hydroxyl; alkyl radicals substituted with at least one amino;carboxyl radicals; and carbamoyl radicals. By way of non-limitingexample, mention may be made of when R is chosen from hydrogen and fromat least one radical chosen from hydroxyl, methyl, amino, hydroxymethyl,and aminomethyl radicals. In one embodiment, R is hydrogen.

In formula (I) above, for instance, b may be equal to 0, or R₄ may bechosen from alkyl radicals; alkyl radicals substituted with at least onehydroxyl; alkyl radicals substituted with at least one amino; carboxylradicals; and carbamoyl radicals. For example, R₄ may be hydrogen.

In formula (I) above, R₃ may be, for instance, chosen from hydrogen;hydroxyl radicals; amino radicals; alkyl radicals; alkyl radicalssubstituted with at least one hydroxyl; alkyl radicals substituted withat least one amino; carboxyl radicals; and carbamoyl radicals. Forexample, R₃ may be hydrogen.

The carbon substituted with R₃ or with R₄ may be of (R) and (S)configuration.

The counterions Y⁻ may be chosen, for example, from a halogen atom, ahydroxide, a hydrogen sulphate, an acetate, a tartrate and a(C₁–C₆)alkyl sulphate. For instance, Y⁻ may be chosen from a methylsulphate and an ethyl sulphate.

Non-limiting examples of derivatives of formula (I) that may bementioned include:

Formula Nomenclature

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-iumchloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}-1-methyl-3H-imidazol-1-iumchloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]propyl}-trimethylammoniumchloride

{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}trimethylammoniumchloride

1-{3-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]propyl}-1-methylpyrrolidiniumchloride

{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}-(2-hydroxyethyl)dimethylammoniumchloride

{3-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}dimethyl(ethyl-2-methyl-3H-imidazol-1-iumchloride)ammonium; chloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]propyl}-1-methyl-3H-imidazol-1-iumchloride

{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}dimethyl-(3-trimethylsilanyl-propyl)ammonium;chloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}-1-(3-trimethylsilanyl-propyl)-3H-imidazol-1-iumchloride

3-{2-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-iumchloride

3-{2-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]ethyl}-1-methyl-3H-imidazol-1-iumchloride

{3-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]-propyl}trimethylammoniumchloride

{2-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]ethyl}-trimethylammoniumchloride

{3-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]-propyl}-1-methyl-3H-imidazol-1-iumchloride

{2-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]ethyl}(2-hydroxyethyl)-dimethylammoniumchloride

{3-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]ethyl}-dimethyl(ethyl-2-methyl-3H-imidazol-1-iumchloride)ammoniumchloride

1-{3-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]propyl}-1-methyl-pyrrolidinium;chloride

{2-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]ethyl}-dimethyl(3-trimethylsilanylpropyl)ammoniumchloride

3-{2-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]ethyl}-1-(3-trimethylsilanylpropyl)-3H-imidazol-1-iumchloride

{3-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]-2-hydroxy-propyl}trimethylammonium;chloride

{3-[4-(4-Amino-methylphenyl)[1,4-diazepan-1-yl]-2-hydroxypropyl}trimethylammonium;chloride

3-{2-[4-(4-Amino-phenyl)piperazin-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-iumchloride

{3-[4-(4-Amino-phenyl)piperazin-1-yl]-2-hydroxypropyl}trimethylammoniumchloride

3-{2-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-iumchloride

3-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]-2-hydroxypropyl}-trimethylammoniumchloride

3-{2-[4-(4-Amino-3-phenyl)piperazin-1-yl]ethyl}-1-methyl-3H-imidazol-1-iumchloride

{3-[4-(4-Amino-3-phenyl)piperazin-1-yl]propyl}trimethylammonium chloride

3-{2-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]ethyl}-1-methyl-3H-imidazol-1-iumchloride

{3-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]-propyl}trimethylammoniumchloride

1-{3-[4-(4-Amino-phenyl)piperazin-1-yl]propyl}-1-methylpyrrolidiniumchloride

1-{3-[4-(4-Amino-3-phenyl)piperazin-1-yl]propyl}-1-methylpyrrolidiniumchloride

For example, the derivatives of formula (I) may be chosen from:

-   3-{2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-ium    chloride-   3-{2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]ethyl}-1-methyl-3H-imidazol-1-ium    chloride-   {3-[4-(4-aminophenyl)[1,4]diazepan-1-yl]propyl}trimethylammonium    chloride-   {2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]ethyl}trimethylammonium    chloride-   1-{3-[4-(4-aminophenyl)[1,4]diazepan-1-yl]propyl}-1-methylpyrrolidinium    chloride-   {2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]ethyl}(2-hydroxyethyl)dimethylammonium    chloride-   3-{2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]propyl}-1-methyl-3H-imidazol-1-ium    chloride-   {3-[4-(4-aminophenyl)[1,4]diazepan-1-yl]-2-hydroxypropyl}trimethylammonium    chloride-   3-{2-[4-(4-aminophenyl)piperazin-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-ium    chloride-   {3-[4-(4-aminophenyl)piperazin-1-yl]-2-hydroxypropyl}trimethylammonium    chloride-   3-{2-[4-(4-aminophenyl)piperazin-1-yl]ethyl}-1-methyl-3H-imidazol-1-ium    chloride-   {3-[4-(4-aminophenyl)piperazin-1-yl]propyl}trimethylammonium    chloride-   1-{3-[4-(4-aminophenyl)piperazin-1-yl]propyl}-1-methylpyrrolidinium    chloride.

The compounds of formula (I) may be obtained, for example, from thesyntheses described in Patent Application FR 2,828,488.

The cationic compounds of formula (I) may be obtained via the followingsynthetic route:

Another aspect of the present invention is also the nitro compounds thatare useful in the synthesis of the compounds of formula (I). These nitrocompounds correspond to formula (I′)

wherein R₁, R₂, R₃, R₄, a, b and c are as defined above.

The dye composition of the present disclosure comprises, in a mediumthat is suitable for dyeing keratin fibers, such as human hair, at leastone derivative of formula (I) as defined above as an oxidation base.

The at least one oxidation base of the present disclosure may be presentin the composition in an amount, for each oxidation base, if there aremore than one, ranging from about 0.001% to about 10% by weight,relative to the total weight of the dye composition, such as from about0.005% to about 6%.

The dye composition of the present disclosure may comprise at least onecoupler conventionally used for dyeing keratin fibers. Among thesecouplers that may be mentioned, for example, are meta-phenylenediamines,meta-aminophenols, meta-diphenols, naphthalene-based couplers,heterocyclic couplers, and the addition salts thereof.

Non-limiting examples of couplers that may be mentioned include2-methyl-5-aminophenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol,6-chloro-2-methyl-5-aminophenol, 3-aminophenol, 1,3-dihydroxybenzene,1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene,2,4-diamino-1-(β-hydroxyethyloxy)benzene,2-amino-4-(β-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene,1,3-bis(2,4-diaminophenoxy)propane, 3-ureidoaniline,3-ureido-1-dimethylaminobenzene, sesamol,1β-hydroxyethylamino-3,4-methylenedioxybenzene, α-naphthol,2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole,4-hydroxy-N-methylindole, 2-amino-3-hydroxypyridine,6-hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxypyridine,1-N-(β-hydroxyethyl)amino-3,4-methylenedioxybenzene,2,6-bis(β-hydroxyethylamino)toluene, and the acid addition saltsthereof.

In the dye composition disclosed herein, the at least one coupler may bepresent in the dye composition in an amount ranging from about 0.001% toabout 10% by weight, relative to the total weight of the dyecomposition, such as ranging from about 0.005% to about 6%.

The composition of the present disclosure may also optionally compriseat least one additional oxidation base conventionally used in oxidationdyeing, other than theose of formula (I). By way of example, theoptional at least one additional oxidation base may be chosen frompara-phenylenediamines other than those described above,bis(phenyl)alkylenediamines, para-aminophenols, bis-para-aminophenols,ortho-aminophenols, heterocyclic bases, and the addition salts thereof.

For example, without limitation, among the optional at least oneadditional para-phenylenediamine mention may be made ofpara-phenylenediamine, para-tolylenediamine,2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine,2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine,2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine,N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine,4-amino-N,N-diethyl-3-methylaniline,N,N-bis(β-hydroxyethyl)-para-phenylenediamine,4-N,N-bis(β-hydroxyethyl)amino-2-methylaniline,4-N,N-bis(β-hydroxyethyl)amino-2-chloroaniline,2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine,2-isopropyl-para-phenylenediamine,N-(β-hydroxypropyl)-para-phenylenediamine,2-hydroxymethyl-para-phenylenediamine,N,N-dimethyl-3-methyl-para-phenylenediamine,N-ethyl-N-(β-hydroxyethyl)-para-phenylenediamine,N-(β,γ-dihydroxypropyl)-para-phenylenediamine,N-(4′-aminophenyl)-para-phenylenediamine,N-phenyl-para-phenylenediamine,2-β-hydroxyethyloxy-para-phenylenediamine,2-β-acetylaminoethyloxy-para-phenylenediamine,N-(β-methoxyethyl)-para-phenylenediamine, 4-aminophenylpyrrolidine,2-thienyl-para-phenylenediamine, 2-β-hydroxyethylamino-5-aminotolueneand 3-hydroxy-1-(4′-aminophenyl)pyrrolidine, and the acid addition saltsthereof.

Among the para-phenylenediamines mentioned above, for example,para-phenylenediamine, para-tolylenediamine,2-isopropyl-para-phenylenediamine,2-β-hydroxyethyl-para-phenylenediamine,2-β-hydroxyethyloxy-para-phenylenediamine,2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine,2,3-dimethyl-para-phenylenediamine,N,N-bis(p-hydroxyethyl)-para-phenylenediamine,2-chloro-para-phenylenediamine,2-β-acetylaminoethyloxy-para-phenylenediamine, and the acid additionsalts thereof may be used.

Among the bis(phenyl)alkylenediamines that may be used, non-limitingmention may be made, for example, ofN,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol,N,N′-bis(p-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-ethylenediamine,N,N′-bis(4-aminophenyl)tetramethylenediamine,N,N′-bis(β-hydroxyethyl)N,N′-bis(4-aminophenyl)tetramethylenediamine,N,N′-bis(4-methylaminophenyl) tetramethylenediamine,N,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine,1,8-bis(2,5-diaminophenoxy)-3,6-dioxaoctane, and the acid addition saltsthereof.

Among the para-aminophenols which may be used, non-limiting mention maybe made, for example, of para-aminophenol, 4-amino-3-methylphenol,4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol,4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol,4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol,4-amino-2-(β-hydroxyethylaminomethyl)phenol, 4-amino-2-fluorophenol, andthe acid addition salts thereof.

Among the ortho-aminophenols which can be used, non-limiting mention maybe made, for example, of 2-aminophenol, 2-amino-5-methylphenol,2-amino-6-methylphenol, 5-acetacarbamoyl-2-aminophenol, and the acidaddition salts thereof.

Among the heterocyclic bases that may be used, non-limiting mention maybe made, for example, of pyridine derivatives, pyrimidine derivativesand pyrazole derivatives.

Among the pyridine derivatives that may be used, non-limiting mentionmay be made of the compounds described, for example, in patents GB1,026,978 and GB 1,153,196, as well as 2,5-diaminopyridine;2-(4-methoxyphenyl)amino-3-aminopyridine; 2,3-diamino-6-methoxypyridine;2-(β-methoxyethyl)amino-3-amino-6-methoxypyridine; 3,4-diaminopyridine;and the acid addition salts thereof.

Other pyridine oxidation bases that may be useful in the present dyecomposition as disclosed herein are the 3-aminopyrazolo[1,5-a]pyridineoxidation bases and the addition salts thereof described, for example,in patent application FR 2,801,308. By way of example, non-limitingmention may be made of pyrazolo[1,5-a]pyrid-3-ylamine;2-acetylaminopyrazolo[1,5-a]pyrid-3-ylamine;2-morpholin-4-ylpyrazolo[1,5-a]pyrid-3-ylamine;3-aminopyrazolo[1,5-a]pyridine-2-carboxylic acid,2-methoxypyrazolo[1,5-a]pyrid-3-ylamine;(3-aminopyrazolo[1,5-a]pyrid-7-yl)methanol;2-(3-aminopyrazolo[1,5-a]pyrid-5-yl)ethanol;2,3-aminopyrazolo[1,5-a]pyrid-7-yl)ethanol;(3-aminopyrazolo[1,5-a]pyrid-2-yl)methanol;3,6-diaminopyrazolo[1,5-a]pyridine; 3,4-diaminopyrazolo[1,5-a]pyridine;pyrazolo[1,5-a]pyridine-3,7-diamine;7-morpholin-4-ylpyrazolo[1,5-a]pyrid-3-ylamine;pyrazolo[1,5-a]pyridine-3,5-diamine;5-morpholin-4-ylpyrazolo[1,5-a]pyrid-3-ylamine;2-[(3-aminopyrazolo[1,5-a]pyrid-5-yl)(2-hydroxyethyl)amino]ethanol;2-[(3-aminopyrazolo[1,5-a]pyrid-7-yl) (2-hydroxyethyl)amino]ethanol;3-aminopyrazolo[1,5-a]pyrid-5-ol; 3-aminopyrazolo[1,5-a]pyrid-4-ol;3-aminopyrazolo[1,5-a]pyrid-6-ol; 3-aminopyrazolo[1,5-a]pyrid-7-ol andalso the addition salts thereof with an acid or with a base.

Among the pyrimidine compounds which may be used, non-limiting mentionmay be made of the compounds described, for example, in German Patent DE2,359399, or Japanese Patents JP 88-169,571; JP 05,63,124; EP 0,770,375or patent application WO 96/15765, such as 2,4,5,6-tetraminopyrimidine,4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine,2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine. Amongthe pyrazolopyrimidine derivatives that may be used, non-limitingmention may be made for instance, of those mentioned in patentapplication FR-A-2,750,048 and among which mention may be made ofpyrazolo[1,5-a]pyrimidine-3,7-diamine;2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;pyrazolo[1,5-a]pyrimidine-3,5-diamine;2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine;3-aminopyrazolo[1,5-a]pyrimidin-7-ol;3-aminopyrazolo[1,5-a]pyrimidin-5-ol;2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol;2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol;2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyethyl)amino]ethanol;2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)(2-hydroxyethyl)amino]ethanol;5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; 2,5, N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;3-amino-5-methyl-7-imidazolylpropylaminopyrazolo[1,5-a]pyrimidine; andthe acid addition salts thereof and the tautomeric forms thereof, when atautomeric equilibrium exists.

Among the pyrazole derivatives that may be used, non-limiting mentionmay be made of the compounds described in patents DE 3,843,892 and DE4,133,957 and patent applications WO 94/08969, WO 94/08970,FR-A-2,733,749 and DE 195,43,988, such as 4,5-diamino-1-methylpyrazole;4,5-diamino-1-(β-hydroxyethyl)pyrazole; 3,4-diaminopyrazole;4,5-diamino-1-(4′-chlorobenzyl)pyrazole;4,5-diamino-1,3-dimethylpyrazole; 4,5-diamino-3-methyl-1-phenylpyrazole;4,5-diamino-1-methyl-3-phenylpyrazole;4-amino-1,3-dimethyl-5-hydrazinopyrazole;1-benzyl-4,5-diamino-3-methylpyrazole;4,5-diamino-3-tert-butyl-1-methylpyrazole;4,5-diamino-1-tert-butyl-3-methylpyrazole;4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole;4,5-diamino-1-ethyl-3-methylpyrazole;4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole;4,5-diamino-1-ethyl-3-hydroxymethylpyrazole;4,5-diamino-3-hydroxymethyl-1-methylpyrazole;4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole;4,5-diamino-3-methyl-1-isopropylpyrazole;4-amino-5-(2′-aminoethyl)amino-1,3-dimethylpyrazole;3,4,5-triaminopyrazole; 1-methyl-3,4,5-triaminopyrazole;3,5-diamino-1-methyl-4-methylaminopyrazole;3,5-diamino-4-(β-hydroxyethyl)amino-1-methylpyrazole; and the acidaddition salts thereof.

As defined above, the optional at least one additional oxidation base,when present, is present in an amount, for each additional oxidationbase, ranging from about 0.001% to about 10% by weight relative to thetotal weight of the dye composition, for example, from about 0.005% toabout 6%.

The addition salts of the oxidation bases and of the couplers that maybe used in the dye compositions disclosed herein may be chosen from, forexample, the addition salts with an acid, such as the hydrochlorides,hydrobromides, sulphates, citrates, succinates, tartrates, lactates,tosylates, benzenesulphonates, phosphates and acetates; and the additionsalts with a base, such as sodium hydroxide, potassium hydroxide,ammonia, amines and alkanolamines.

The dye composition in accordance with the present disclosure may alsocomprise at least one direct dye that may be chosen from for example,nitrobenzene dyes, azo direct dyes and methine direct dyes. The directdyes may be of nonionic, anionic or cationic nature.

A medium suitable for dyeing, also known as the dye support, compriseswater or a mixture of water and at least one organic solvent to dissolvethe compounds that would not be sufficiently soluble in water. Among theorganic solvents that may be used, non-limiting mention may be made, forexample, of C₁–C₄ lower alkanols, such as ethanol and isopropanol;polyols and polyol ethers such as 2-butoxyethanol, propylene glycol,propylene glycol monomethyl ether, diethylene glycol monoethyl ether andmonomethyl ether, as well as aromatic alcohols such as benzyl alcohol,phenoxyethanol, and mixtures thereof.

The at least one solvent may be present in the dye composition in anamount, for example, ranging from about 1% to about 40% by weight,relative to the total weight of the dye composition, such as rangingfrom about 5% to about 30% by weight.

The dye composition in accordance with the present disclosure can alsocomprise various adjuvants conventionally used in compositions fordyeing the hair, such as anionic, cationic, nonionic, amphoteric, andzwitterionic surfactants and mixtures thereof; anionic, cationic,nonionic, amphoteric, and zwitterionic polymers, and mixtures thereof;inorganic or organic thickeners, for instance, anionic, cationic,nonionic and amphoteric associative polymeric thickeners, antioxidants,penetration agents, sequestering agents, fragrances, buffers, dispersingagents, packaging agents such as, for example, silicones, which may ormay not be volatile or modified, film-forming agents, ceramides,preserving agents and opacifiers.

The above adjuvants may be present in the dye composition in an amountfor each of them ranging from about 0.01% to about 20% by weight,relative to the total weight of the dye composition.

Needless to say, a person skilled in the art will take care to selectany of the optional additional compounds such that the advantageousproperties intrinsically associated with the oxidation dye compositionin accordance with the present disclosure are not, or are notsubstantially, adversely affected by the addition envisaged.

The pH of the dye composition in accordance with the present disclosuremay range from about 3 to about 12, such as from about 5 to about 11. Itmay be adjusted to the desired value using acidifying or basifyingagents usually used in the dyeing of keratin fibers, or alternativelyusing standard buffer systems.

Among the acidifying agents that may be used, non-limiting mention maybe made, for example, of inorganic and organic acids such ashydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylicacids such as acetic acid, tartaric acid, citric acid, lactic acid, andsulphonic acids.

Among the basifying agents that may be used, non-limiting mention may bemade, for example, of aqueous ammonia, alkaline carbonates,alkanolamines such as mono-, di- and triethanolamine and derivativesthereof, sodium hydroxide, potassium hydroxide and the compounds offormula (V):

wherein W is a propylene residue that may be unsubstituted, orsubstituted with a hydroxyl group or a C₁–C₄ alkyl radical; R_(a),R_(b), R_(c) and R_(d), which may be identical or different, are chosenfrom a hydrogen atom, C₁–C₄ alkyl radicals and C₁–C₄ hydroxyalkylradicals.

The dye composition according to the present disclosure may be invarious forms, such as liquids, creams and gels, or in any other formthat is suitable for dyeing keratin fibers, such as human hair.

The process of the present disclosure is a process wherein the dyecomposition as described above is applied to the fibers, and the coloris developed using an oxidizing agent. The color may be developed atacidic, neutral or alkaline pH and the oxidizing agent may be added tothe composition as disclosed herein just at the time of use, or it maybe used starting with an oxidizing composition comprising it, which isapplied simultaneously or sequentially to the composition of theinvention.

According to one aspect, the dye composition according to the presentdisclosure is mixed, for example, at the time of use, with a compositioncomprising, in a medium that is suitable for dyeing, at least oneoxidizing agent, this oxidizing agent being present in an amount that issufficient to develop a coloration. The mixture obtained is then appliedto keratin fibers. After an action time of 3 to 50 minutesapproximately, such as 5 to 30 minutes approximately, the keratin fibersare rinsed, washed with shampoo, rinsed again and then dried.

The oxidizing agents conventionally used for the oxidation dyeing ofkeratin fibers include, for example, hydrogen peroxide, urea peroxide,alkali metal bromates, persalts such as perborates and persulphates,peracids and oxidase enzymes, among which, non-limiting mention may bemade of peroxidases, 2-electron oxidoreductases such as uricases, and4-electron oxygenases, for instance laccases. For example, the oxidizingagent may be hydrogen peroxide.

The oxidizing composition may also comprise various adjuvantsconventionally used in compositions for dyeing the hair and as definedabove.

The pH of the oxidizing composition comprising the oxidizing agent issuch that, after mixing with the dye composition, the pH of theresulting composition applied to the keratin fibers ranges for example,from about 3 to about 12, for instance from about 5 to about 11. The pHmay be adjusted to the desired value by means of acidifying or basifyingagents usually used in the dyeing of keratin fibers and as definedabove.

The ready-to-use composition that is finally applied to the keratinfibers may be in various forms, such as in the form of liquids, creams,gels, or any other form that is suitable for dyeing keratin fibers, suchas human hair.

Another aspect of the present disclosure is a multi-compartment dyeingdevice or “kit,” in which at least one first compartment contains thedye composition as disclosed herein, and at least one second compartmentcontains an oxidizing composition. This device may be equipped with ameans for applying the desired mixture to the hair, such as the devicesdescribed in patent FR-2,586,913 in the name of L'Oreal.

Using this device, it is possible to dye keratin fibers using a processthat includes mixing a dye composition comprising at least one oxidationbase of formula (I) with an oxidizing agent, and applying the mixtureobtained to the keratin fibers for a time that is sufficient to developthe desired coloration.

Other than in the examples, or where otherwise indicated, all numbersexpressing quantities of ingredients, reaction conditions, and so forthused in the specification and claims are to be understood as beingmodified in all instances by the term “about.” Accordingly, unlessindicated to the contrary, the numerical parameters set forth in thefollowing specification and attached claims are approximations that mayvary depending upon the desired properties sought to be obtained herein.At the very least, and not as an attempt to limit the application of thedoctrine of equivalents to the scope of the claims, each numericalparameter should be construed in light of the number of significantdigits and ordinary rounding approaches.

Notwithstanding that the numerical ranges and parameters setting forththe broad scope are approximations, the numerical values set forth inthe specific examples are reported as precisely as possible. Anynumerical value, however, inherently contain certain errors necessarilyresulting from the standard deviation found in their respective testingmeasurements. The following examples are intended to illustrate theinvention without limiting the scope as a result.

EXAMPLES Example 1 Preparation of3-{2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-iumchloride dihydrochloride (4)

1^(st) Step: Synthesis of2-chloro-1-[4-(4-nitrophenyl)[1,4]diazepan-1-yl]ethanone (2)

22.1 g (0.1 mol) of 1-(4-nitrophenyl)[1,4]diazepane, 8.3 g (0.06 mol) ofpotassium carbonate and 120 ml of dimethylformamide were mixed togetherin a reactor. 8.3 ml (0.11 mol) of chloroacetyl chloride were added tothis stirred suspension, while maintaining the temperature between 15and 25° C. After stirring for about ten hours at room temperature, 400 gof slightly hydrochloric ice-cold water were added to the mixture: ayellow gum crystallized. After filtering off by suction, washing withwater and drying under vacuum over phosphorus pentoxide, 22.4 g ofyellow crystals were obtained (yield=75%).

¹H NMR (400 MHz, DMSO D6): 1.83 (m), 1.9 (m), 3.37 (t), 3.47 (t), 3.67(m), 3.85 (t), 4.28 (s), 4.36 (s), 6.9 (m), 8.04 (m).

2^(nd) Step: Synthesis of3-methyl-1-{2-[4-(4-nitrophenyl)[1,4]diazepan-1-yl]-2-oxoethyl}-3H-imidazol-1-iumchloride (3)

A mixture of 19.95 g (0.067 mol) of2-chloro-1-[4-(4-nitrophenyl)[1,4]diazepan-1-yl]ethanone obtained abovein the preceding step and 11.5 g (0.14 mol) of 1-methyl-1H-imidazole in40 ml of isobutanol were refluxed for 1 hour 30 minutes with stirring.After crystallization under cold conditions, a precipitate of yellowcrystals was obtained. This precipitate was then washed with isobutanoland then with ethyl ether and dried at 40° C. under vacuum and overphosphorus pentoxide.

After recrystallization from 65 ml of refluxing ethanol, 14.0 g of ayellow crystalline compound were obtained (yield=55%).

¹H NMR (400 MHz, DMSO D6): 1.85–2 (2m, 2H), 3.37–3.5 (2m, 2H),3.72–3.89–3.95 (2 m+2s, 9H), 5.385–5.389 (2s, 2H), 6.93 (2m, 2H), 7.61(2dd, 1H), 7.68 (2dd, 1H), 8.05 (2m, 2H), 9.08–9.1 (2dd, 1H).

3^(rd) Step: Synthesis of3-[2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]-2-oxymethyl]-1-methyl-3H-imidazol-1-iumchloride dihydrochloride (4)

13.1 g (0.0345 mol) of3-methyl-1-{2-[4-(4-nitrophenyl)[1,4]diazepan-1-yl]-2-oxoethyl)-3H-imidazol-1-iumchloride, obtained in the preceding step, 3 g of palladium-on-charcoal(containing 50% water), 400 ml of 960 ethanol and 150 ml of water wereplaced in a one-liter hydrogenator.

The reduction was performed over two hours under a hydrogen pressure ofabout five bar and at a temperature of 70° C. After filtering off thecatalyst under nitrogen, aqueous hydrochloric acid was poured onto themixture.

After evaporating the filtrate under reduced pressure, recrystallizingthe mixture from refluxing ethanol, hydrochloric acid, and water, anddrying at 40° C. under vacuum and over potassium hydroxide, 15.9 g(yield=75%) of white crystals were obtained.

The elemental analysis calculated for C₁₇H₂₆N₅OCl₃+H₂O+CH₃CH₂OH was:

C % H % N % O % Cl % Calculated: 48.87 7.04 14.38 9.86 21.85 Found:46.82 6.89 14.42 9.41 22.39

The ¹³C NMR and ¹H NMR spectra were in accordance with the expectedstructure.

¹H NMR (400 MHz, D₂O): 2.21–2.47 (2m, 2H), 3.78–3.89 (m, 4H), 3.97–4.09(m+s, 7H), 5.27–5.42 (2H), 7.33–7.72 (m, 6H), 8.71–8.8 (2s, 1H). ¹³C NMR(D₂O): 23.25; 24.32; 35.89; 41.77; 43.44; 44.96; 45.42; 50.17; 53.98;55.94; 54.59; 56.5; 118.25; 120.69; 123.1; 123.27; 123.55; 123.68;124.9; 124.99; 125.53; 128.71; 137; 143.6; 144.8; 166.16; 166.74.

The mass spectrum showed that the expected cation, C₁₇H₂₄N₅O⁺, is mainlydetected at m/z=314 in ES+.

Example 22-hydroxy-N,N,N-trimethyl-3-[4-(4-aminophenyl)-1,4-diazepan-1-yl]propan-1-aminiumacetate (3)

Synthesis of 2-hydroxy-N,N,N-trimethyl-3-[4-(4-nitrophenyl)-1,4-diazepan-1-yl]propan-1-aminiumacetate (2)

1.1 g of 1-(4-nitrophenyl)-1,4-diazepane (0.005 mol), 3 ml of DMF and0.76 g (0.00448 mol) of glycidyltrimethylammonium were placed in athree-necked flask. The mixture was heated at 105° C. for 20 hours. Thereaction mixture was then poured into 50 ml of ethyl acetate. Aftertriturating the gum and removing the ethyl acetate, the product wastaken up in water and extracted with butanol, and the aqueous phase wasconcentrated. A sample was purified by preparative HPLC.

¹H NMR (DMSO d₆, 200 MHz, ppm) was in accordance with the expectedproduct: 8.03 (d, 2H); 6.84 (d, 2H); 4.25 (m, 1H); 3.23–3.67 (m, 8H);3.095 (s, 9H); 2.823 (m, 2H); 2.5–2.615 (m, 2H); 1.83 (m, 2H); 1.69 (s,3H). Mass ESI⁺: m/z=337[M⁺].

Synthesis of2-hydroxy-N,N,N-trimethyl-3-[4-(4-aminophenyl)-1,4-diazepan-1-yl]propan-1-aminiumacetate (3)

After reduction with zinc/acetic acid,2-hydroxy-N,N,N-trimethyl-3-[4-(4-aminophenyl)-1,4-diazepan-1-yl]propan-1-aminiumacetate was obtained.

Mass ESI⁺: m/z=307[M⁺].

EXAMPLES OF DYEING Examples 1 to 7 Dyeing in alkaline medium using3-{2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-ium ChlorideDihydrochloride

The dye compositions below were prepared:

Examples 1 2 3 4 5 6 7 3-{2-[4-(4-Aminophenyl) 10⁻³ mol 10⁻³ mol 10⁻³mol — — — — [1,4]diazepan-1-yl]-2- oxoethyl}-1-methyl-3H- imidazol-1-iumchloride dihydrochloride (base) 2-Hydroxy-N,N,N- — — — 10⁻³ mol 10⁻³ mol10⁻³ mol 10⁻³ mol trimethyl-3-[4-(4-amino phenyl)-1,4-diazepan-1-yl]propan-1-aminium acetate (base) 2-(2,4-Diaminophenoxy) 10⁻³ mol — —10⁻³ mol — — — ethanol dihydrochloride (coupler) 3-Amino-2-chloro-6- —10⁻³ mol — — 10⁻³ mol — — methylphenol hydrochloride (coupler)3,6-Dimethyl-1H- — — 10⁻³ mol — — 10⁻³ mol — pyrazolo [5,1-c]-[1,2,4]triazole (coupler) 2-Methyl-5-aminophenol 10⁻³ mol (coupler) Dyesupport (1) (*) (*) (*) (*) (*) (*) (*) Demineralized water qs 100 g 100g 100 g 100 g 100 g 100 g 100 g (*) Dye support (1) pH 9.5 96° ethylalcohol 20.8 g Sodium metabisulphite as an aqueous 35% solution 0.23 gA.M. Pentasodium salt of diethylene triamine pentacetic acid as anaqueous 40% solution 0.48 g A.M. C₈–C₁₀ alkyl polyglucoside as anaqueous 60% solution  3.6 g A.M. Benzyl alcohol  2.0 g Polyethyleneglycol containing 8  3.0 g ethylene oxide units NH₄Cl 4.32 g Aqueousammonia containing 20% NH₃ 2.94 g

At the time of use, each composition was mixed with an equal weight of20-volumes aqueous hydrogen peroxide solution (6% by weight). A final pHof 9.5 was obtained.

Each mixture obtained was applied to locks of grey hair containing 90%white hairs. After a leave-in time of 30 minutes, the locks were rinsed,washed with a standard shampoo, rinsed again and then dried.

The following dyeing results were obtained.

Ex- amples 1 2 3 4 5 6 7 Shade Blue Blue- Chromatic Blue Blue- ChromaticGrey- ob- violet red-violet violet red-violet violet served

Examples 8 to 16 Dyeing in acidic medium using3-(2-[4-(4-aminophenyl)[1,4]diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-iumchloride dihydrochloride

The following dye compositions were prepared:

Examples 8 9 10 11 3-{2-[4-(4-Amino- 10⁻³ mol 10⁻³ mol 10⁻³ mol 10⁻³ molphenyl)[1,4]diazepan-1-yl]- 2-oxoethyl}-1-methyl-3H- imidazol-1-iumchloride; dihydrochloride (base) 2-(2,4-Diaminophenoxy)- 10⁻³ molethanol dihydrochloride (coupler) 3-Amino-2-chloro-6- 10⁻³ molmethyphenol hydrochloride (coupler) 2-Methyl-5-aminophenol 10⁻³ mol(coupler) 2-Aminopyridin-3-ol 10⁻³ mol (coupler) Dye support (2) (*) (*)(*) (*) Demineralized water qs 100 g 100 g 100 g 100 g Examples 12 13 1415 16 2-Hydroxy-N,N,N- 10⁻³ mol 10⁻³ mol 10⁻³ mol 10⁻³ mol 10⁻³ moltrimethyl-3-[4-(4- aminophenyl)-1,4-diazepan- 1-yl]propan-1- aminiumacetate (base) 2-(2,4-Diamino- 10⁻³ mol — — — — phenoxy)ethanoldihydrochloride (coupler) 3-Amino-2-chloro-6- — 10⁻³ mol — — —methyphenol hydrochloride (coupler) 2-Methyl-5-aminophenol — — 10⁻³ mol— — (coupler) 2-Aminopyridin-3-ol — — — 10⁻³ mol — (coupler)6-Hydroxy-1-H-indole — — — — 10⁻³ mol (coupler) Dye support (2) (*) (*)(*) (*) (*) Demineralized water qs 100 g 100 g 100 g 100 g 100 g (*) Dyesupport (2) pH 7 96° ethyl alcohol 20.8 g Sodium metabisulphite as anaqueous 35% solution 0.23 g A.M. Pentasodium salt of diethylene triaminepentacetic acid as an aqueous 40% solution 0.48 g A.M. C₈–C₁₀ alkylpolyglucoside as an aqueous 60% solution  3.6 g A.M. Benzyl alcohol  2.0g Polyethylene glycol containing 8  3.0 g ethylene oxide units Na₂HPO₄0.28 g KH₂PO₄ 0.46 g

At the time of use, each composition was mixed with an equal weight of20-volumes aqueous hydrogen peroxide solution (6% by weight). A final pHof 7 was obtained.

Each mixture obtained was applied to locks of grey hair containing 90%white hairs. After a leave-in time of 30 minutes, the locks were rinsed,washed with a standard shampoo, rinsed again and then dried.

The following dyeing results were obtained.

Examples 8 9 10 11 12 13 14 15 16 Shade Violet-blue Blue-violet VioletGrey-violet Blue Violet Brown-violet Brown-grey Brown-grey observed

1. A compound of formula (I), and the addition salts thereof

wherein: a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R₁ may be identical or different, b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R₄ may be identical or different, c is equal to 0 or 1, R₁ is chosen from a halogen atom; C₁–C₈ aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO₂ group; and an onium radical Z; with the proviso that the radical R₁ does not comprise a peroxide bond or diazo, nitro or nitroso radicals, R₂ comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical, R₃ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyl radical; a hydroxyalkyl radical; an alkoxy radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an amino radical; a monoalkylamino radical; a dialkylamino radical; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical; R₄ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyalkyl radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical.
 2. The compound according to claim 1, wherein R₁ is chosen from C₁–C₄ alkyl radicals, C₁–C₄ alkoxyalkyl radicals, C₁–C₄ hydroxyalkyl radicals, C₁–C₄ aminoalkyl radicals, C₁–C₄ alkoxy radicals, C₁–C₄ hydroxyalkoxy radicals, and C₁–C₄ carboxyalkyl radicals.
 3. The compound according to claim 2, wherein R₁ is chosen from methyl, hydroxymethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, methoxy, isopropyloxy and 2-hydroxyethoxy radicals.
 4. The compound according to claim 1, wherein a is equal to 0 or
 1. 5. The compound according to claim 1, wherein R₂ is an onium radical Z of formula (II)

wherein: D is a linker arm chosen from a covalent bond and from linear and branched C₁–C₁₄ alkylene chains, which may comprise at least one hetero atom chosen from oxygen, sulphur and nitrogen, and which may be substituted with at least one radical chosen from hydroxyl and amino radicals, and which may further optionally comprise at least one carbonyl radical; R₈, R₅ and R₆, which may be identical or different, are each separately chosen from C₁–C₁₅ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; (C₁–C₆)alkoxy(C₁–C₆)alkyl radicals; aryl radicals; benzyl radicals; C₁–C₆ carbamoylalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals wherein the amine is mono- or disubstituted with at least one radical chosen from C₁–C₄ alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; and quaternary ammonium radicals; R₈, R₅ and R₆ together, in pairs, form, with the nitrogen atom to which they are attached, a saturated 4-, 5-, 6- or 7-membered carbon-based ring optionally comprising at least one hetero atom, wherein the ring may optionally be substituted with a radical chosen from hydroxyl radicals, C₁–C₆ alkyl radicals, C₁–C₆ monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoyl radicals, carboxyl radicals, (C₁–C₆)alkylcarbonyl radicals, amino radicals, and amino radicals mono- and disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; R₇ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals wherein the amine is mono- or disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carboxyalkyl radicals; C₁–C₆ carbamoylalkyl radicals; C₁–C₆ trifluoroalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆ sulphonamidoalkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; (C₁–C₆)alkylsulphinyl(C₁–C₆)alkyl radicals; (C₁–C₆)alkylsulphonyl(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; N—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals; and N—(C₁–C₆)alkylsulphonamido(C₁–C₆)alkyl radicals; x is equal to 0 or 1, with the proviso that when x=0, then the linker arm D is attached to the nitrogen atom bearing the radicals R₅, R₆ and R₈, when x=1, then two of the radicals R₅, R₆ and R₈ form, together with the nitrogen atom to which they are attached, a 4-, 5-, 6- or 7-membered saturated ring and the linker arm D is linked to a carbon atom of the saturated ring; Y⁻ is a counterion.
 6. The compound according to claim 5, wherein: x is equal to 0, and R₅, R₆ and R₈ are each separately chosen from C₁–C₆ alkyl radicals, C₁–C₄ monohydroxyalkyl radicals, C₂–C₄ polyhydroxyalkyl radicals, (C₁–C₆)alkoxy(C₁–C₄)alkyl radicals, C₁–C₆ carbamoyl alkyl radicals, and tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, or wherein R₈ and R₅ together form a ring chosen from azetidine, pyrrolidine, piperidine, piperazine and morpholine rings, and wherein R₆ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆ aminoalkyl radicals; aminoalkyl radicals mono- and disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carbamoylalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; and N—(C₁–C₆)-alkylcarbamoyl(C₁–C₆)alkyl radicals.
 7. The compound according to claim 5, wherein x is equal to 1; R₇ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals wherein the amine is mono- or disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carbamylalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; and N—(C₁–C₆)alkylcarbamyl(C₁–C₆)alkyl radicals; R₈ and R₅ together form a ring chosen from azetidine, pyrrolidine, piperidine, piperazine and morpholine rings; and R₆ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals wherein the amine is mono- or disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carbamoylalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; and N—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals.
 8. The compound according to claim 5, wherein R₂ comprises a trialkylammonium alkyl radical, and further wherein the alkyl linking R₂ to the ring is optionally substituted with at least one hydroxyl group.
 9. The compound according to claim 5, wherein D is chosen from a covalent bond and an alkylene chain that may optionally be substituted and/or may comprise a carbonyl group.
 10. The compound according to claim 1, wherein R₂ is an onium radical Z of formula (III)

wherein: D is a linker arm chosen from a covalent bond and from linear and branched C₁–C₁₄ alkylene chains that may optionally comprise at least one hetero atom chosen from oxygen, sulphur and nitrogen, and that may be optionally substituted with at least one radical chosen from hydroxyl and amino radicals, and that may further optionally comprise at least one carbonyl radical; the ring members E, G, J and L, which may be identical or different, are chosen from carbon, oxygen, sulphur and nitrogen atoms to form a ring chosen from pyrrole, pyrazole, imidazole, triazole, oxazole, isooxazole, thiazole and isothiazole rings, q is an integer ranging from 1 to 4; R, which may be identical or different, is chosen from a hydrogen atom, halogen atoms, hydroxyl radicals, C₁–C₆ alkyl radicals, C₁–C₆ monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoyl radicals, carboxyl radicals, C₁–C₆ alkylcarbonyl radicals, amino radicals, amino radicals mono- and disubstituted with a radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ monohydroxyalkyl radicals C₂–C₆ polyhydroxyalkyl radicals, and quaternary ammonium radicals; R₇ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁–C₆ aminoalkyl radicals, C₁–C₆ aminoalkyl radicals wherein the amine is substituted with a radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carboxyalkyl radicals; C₁–C₆ carbamoylalkyl radicals; C₁–C₆ trifluoroalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆ sulphonamidoalkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; (C₁–C₆)-alkylsulphinyl(C₁–C₆)alkyl radicals; (C₁–C₆)alkylsulphonyl(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; N—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals; N—(C₁–C₆)alkylsulphonamido(C₁–C₆)alkyl radicals; and quaternary ammonium radicals; x is equal to 0 or 1, with the proviso that when x=0, the linker arm D is attached to the nitrogen atom, when x=1, the linker arm D is attached to one of the ring members E, G, J or L, and Y⁻ is a counterion.
 11. The compound according to claim 10, wherein the ring members E, G, J and L form a ring chosen from pyrrole, imidazole, pyrazole, oxazole, thiazole and triazole rings.
 12. The compound according to claim 11, wherein the ring members E, G, J and L form an imidazole ring.
 13. The compound according to claim 10, wherein x is equal to 0 and D is chosen from a covalent bond and an alkylene chain that may be optionally substituted and/or that may optionally comprise a carbonyl function.
 14. The compound according to claim 10, wherein x is equal to 0 and R is chosen from a hydrogen atom, hydroxyl radicals, C₁–C₆ alkyl radicals, C₁–C₆ monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoyl radicals, C₁–C₆ alkylcarbonyl radicals, amino radicals, amino radicals mono- and disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ monohydroxyalkyl radicals and C₂–C₆ polyhydroxyalkyl radicals.
 15. The compound according to claim 10, wherein x is equal to 1, R₇ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals wherein the amine is mono- or disubstituted with at least one radical chosen from (C₁–C₆)alkyl radicals, (C₁–C₆)alkylcarbonyl radicals, carbamoyl radicals and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carbamoylalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; N—(C₁–C₆)alkylcarbamyl(C₁–C₆)alkyl radicals; and R is chosen from a hydrogen atom, a hydroxyl radical, C₁–C₆ alkyl radicals, C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; carbamoyl radicals; C₁–C₆ alkylcarbonyl radicals; amino radicals; amino radicals mono- and disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals.
 16. The compound according to claim 15, wherein R is chosen from a hydrogen atom and alkyl radicals that may optionally be substituted, and R₇ is an alkyl radical that may optionally be substituted.
 17. The compound according to claim 16, wherein R is chosen from hydrogen; an alkyl radical; alkyl radicals substituted with at least one hydroxyl; alkyl radicals substituted with at least one amino; a carboxyl radical; a carbamoyl radical; an amino radical; and a hydroxyl radical.
 18. The compound according to claim 17, wherein R is chosen from hydrogen; a hydroxyl radical; a methyl radical; an amino radical; a hydroxymethyl radical; and an aminomethyl radical.
 19. The compound according to claim 1, wherein R₂ is an onium radical Z of formula (IV)

wherein: D is a linker arm chosen from a covalent bond and from linear and branched C₁–C₁₄ alkylene chains, which may comprise at least one hetero atom chosen from oxygen, sulphur and nitrogen atoms, and which may optionally be substituted with at least one radical chosen from hydroxyl and amino radicals, and further may optionally comprise at least one carbonyl radical; the ring members E, G, J, L and M, which may be identical or different, are chosen from carbon, oxygen, sulphur and nitrogen atoms and form a ring chosen from pyridine, pyrimidine, pyrazine, triazine and pyridazine rings; m is an integer ranging from 1 to 5; R, which may be identical or different, is chosen from a hydrogen atom, halogen atoms, hydroxyl radicals, C₁–C₆ alkyl radicals, C₁–C₆ monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoyl radicals, carboxyl radicals, C₁–C₆ alkylcarbonyl radicals, amino radicals, amino radicals substituted with a radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ monohydroxy-alkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; and quaternary ammonium radicals; R₇ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁–C₆ aminoalkyl radicals; C₁–C₆ aminoalkyl radicals wherein the amine is mono- or disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carboxyalkyl radicals; C₁–C₆ carbamoylalkyl radicals; C₁–C₆ trifluoroalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; C₁–C₆ sulphonamidoalkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; (C₁–C₆)alkylsulphinyl(C₁–C₆)alkyl radicals; (C₁–C₆)alkylsulphonyl(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarboxy(C₁–C₆)alkyl radicals; N—(C₁–C₆)alkylcarbamoyl(C₁–C₆)alkyl radicals; N—(C₁–C₆)alkylsulphonamido(C₁–C₆)alkyl radicals; and quaternary ammonium radicals; x is equal to 0 or 1, with the proviso that when x=0, the linker arm D is attached to the nitrogen atom, when x=1, the linker arm D is attached to one of the ring members chosen from E, G, J, L and M; and Y⁻ is a counterion.
 20. The compound according to claim 19, wherein the ring members E, G, J, L and M form, with the nitrogen of the ring, a ring chosen from pyridine and pyrimidine rings.
 21. The compound according to claim 19, wherein x is equal to 0, and R is chosen from a hydrogen atom, hydroxyl radicals, C₁–C₆ alkyl radicals, C₁–C₆ monohydroxyalkyl radicals, C₂–C₆ polyhydroxyalkyl radicals, C₁–C₆ alkoxy radicals, tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals, carbamoyl radicals, C₁–C₆ alkylcarbonyl radicals, amino radicals, amino radicals mono- and disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ monohydroxyalkyl radicals and C₂–C₆ polyhydroxyalkyl radicals.
 22. The compound according to claim 19, wherein x is equal to 1; R₇ is chosen from C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆ aminoalkyl radicals, C₁–C₆ aminoalkyl radicals wherein the amine is mono- or disubstituted with at least one radical chosen from (C₁–C₆)alkyl radicals, (C₁–C₆)alkylcarbonyl radicals, carbamoyl radicals, and (C₁–C₆)alkylsulphonyl radicals; C₁–C₆ carbamoylalkyl radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; (C₁–C₆)alkylcarbonyl(C₁–C₆)alkyl radicals; N—(C₁–C₆)alkylcarbamyl(C₁–C₆)alkyl radicals; and R is chosen from a hydrogen atom, hydroxyl radicals, C₁–C₆ alkyl radicals; C₁–C₆ monohydroxyalkyl radicals; C₂–C₆ polyhydroxyalkyl radicals; C₁–C₆ alkoxy radicals; tri(C₁–C₆)alkylsilane(C₁–C₆)alkyl radicals; carbamoyl radicals; C₁–C₆ alkylcarbonyl radicals; amino radicals; amino radicals mono- or disubstituted with at least one radical chosen from (C₁–C₆)alkyl, (C₁–C₆)alkylcarbonyl, carbamoyl and (C₁–C₆)alkylsulphonyl radicals.
 23. The compound according to claim 22, wherein R is chosen from a hydrogen atom and alkyl radicals that may optionally be substituted, and R₇ is an alkyl radical that may optionally be substituted.
 24. The compound according to claim 23, wherein R is chosen from hydrogen; an alkyl radical; alkyl radicals substituted with at least one hydroxyl; alkyl radicals substituted with at least one amino; a carboxyl radical; a carbamoyl radical; an amino radical; and a hydroxyl radical.
 25. The compound according to claim 24, wherein R is chosen from hydrogen and from at least one radical chosen from hydroxyl, methyl, amino, hydroxymethyl and aminomethyl radicals.
 26. The compound according to claim 1, wherein either b is equal to zero, or R₄ is chosen from an alkyl radical; alkyl radicals substituted with at least one hydroxyl; alkyl radicals substituted with at least one amino; a carboxyl radical; and a carbamoyl radical.
 27. The compound according to claim 1, wherein R₃ is chosen from hydrogen; a hydroxyl radical; an amino radical; an alkyl radical; alkyl radicals substituted with at least one hydroxyl; alkyl radicals substituted with at least one amino; a carboxyl radical; and a carbamoyl radical.
 28. The compound according to claim 1, wherein counterion Y⁻ is chosen from halogens, a hydroxide, a hydrogen sulphate, an acetate, a tartrate and (C₁–C₆)alkyl sulphates.
 29. The compound according to claim 1, chosen from the following compounds

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-ium chloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}-1-methyl-3H-imidazol-1-ium chloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]propyl}-trimethylammonium chloride

{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}trimethylammonium chloride

1-{3-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]propyl}-1-methylpyrrolidinium chloride

{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}-(2-hydroxyethyl)dimethylammoniumchloride

{3-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}dimethyl(ethyl-2-methyl-3H-imidazol-1-ium chloride)ammonium; chloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]propyl}-1-methyl-3H-imidazol-1-ium chloride

{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}dimethyl-(3-trimethylsilanyl-propyl)ammonium;chloride

3-{2-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]ethyl}-1-(3-trimethylsilanyl-propyl)-3H-imidazol-1-ium chloride

3-{2-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-ium chloride

3-{2-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]ethyl}-1-methyl-3H-imidazol-1-ium chloride

{3-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]-propyl}trimethylammonium chloride

{2-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]ethyl}-trimethylammonium chloride

{3-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]-propyl}-1-methyl-3H-imidazol-1-ium chloride

{2-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]ethyl}(2-hydroxyethyl)-dimethylammoniumchloride

{3-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]ethyl}-dimethyl(ethyl-2-methyl-3H-imidazol-1-iumchloride)ammonium chloride

1-{3-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]propyl}-1-methyl-pyrrolidinium; chloride

{2-[4-(4-Amino-3-methylphenyl)[1,4]-diazepan-1-yl]ethyl}-dimethyl(3-trimethylsilanylpropyl)ammoniumchloride

3-{2-[4-(4-Amino-3-methylphenyl)[1,4]diazepan-1-yl]ethyl}-1-(3-trimethylsilanylpropyl)-3H-imidazol-1-ium chloride

{3-[4-(4-Amino-phenyl)[1,4]diazepan-1-yl]-2-hydroxy-propyl}trimethylammonium; chloride

{3-[4-(4-Amino-methylphenyl)[1,4-diazepan-1-yl]-2-hydroxypropyl}trimethylammonium; chloride

3-{2-[4-(4-Amino-phenyl)piperazin-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-ium chloride

{3-[4-(4-Amino-phenyl)piperazin-1-yl]-2-hydroxypropyl}trimethylammonium chloride

3-{2-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]-2-oxoethyl}-1-methyl-3H-imidazol-1-ium chloride

3-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]-2-hydroxypropyl}-trimethylammonium chloride

3-{2-[4-(4-Amino-3-phenyl)piperazin-1-yl]ethyl}-1-methyl-3H-imidazol-1-ium chloride

{3-[4-(4-Amino-3-phenyl)piperazin-1-yl]propyl}trimethylammonium chloride

3-{2-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]ethyl}-1-methyl-3H-imidazol-1-ium chloride

{3-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]-propyl}trimethylammonium chloride

1-{3-[4-(4-Amino-phenyl)piperazin-1-yl]propyl}-1-methylpyrrolidinium chloride

1-{3-[4-(4-Amino-3-phenyl)piperazin-1-yl]propyl}-1-methylpyrrolidinium chloride


30. The nitro derivatives of formula (I′)

wherein: a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R₁ may be identical or different, b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R₄ may be identical or different, c is equal to 0 or 1, R₁ is chosen from halogen atoms; C₁–C₈ aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO₂ group; and an onium radical Z; with the proviso that the radical R₁ does not comprise a peroxide bond or diazo, nitro or nitroso radicals, R₂ comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical, R₃ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyl radical; a hydroxyalkyl radical; an alkoxy radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an amino radical; a monoalkylamino radical; a dialkylamino; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical; R₄ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyalkyl radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical.
 31. A dye composition comprising, as oxidation base, at least one compound of formula (I), and the addition salts thereof

wherein: a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R₁ may be identical or different, b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R₄ may be identical or different, c is equal to 0 or 1, R₁ is chosen from halogen atoms; C₁–C₈ aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO₂ group; and an onium radical Z; with the proviso that the radical R₁ does not comprise a peroxide bond or diazo, nitro or nitroso radicals, R₂ comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical, R₃ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyl radical; a hydroxyalkyl radical; an alkoxy radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an amino radical; a monoalkylamino radical; a dialkylamino; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical; R₄ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyalkyl radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical.
 32. The dye composition according to claim 31, further comprising at least one coupler chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers, heterocyclic couplers, and the addition salts thereof.
 33. The composition according to claim 31, comprising at least one additional oxidation base other than the compound of formula (I), chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, and the addition salts thereof.
 34. The composition according to claim 33, wherein, for the at least one compound of formula (I) and for the at least one additional oxidation base, if present, each oxidation base in the dye composition is present in an amount ranging from about 0.001% to about 10% by weight, relative to the total weight of the dye composition.
 35. The dye composition according to claim 32, wherein the at least one coupler is present in the dye composition in an amount ranging from about 0.001% to about 10% by weight, relative to the total weight of the dye composition.
 36. The dye composition according to claim 31, further comprising a cosmetic medium suitable for dyeing keratin fibers.
 37. A process for the oxidation dyeing of keratin fibers, comprising applying a dye composition to the fibers in the presence of at least one oxidizing agent, for a time sufficient to develop a desired coloration, wherein the dye composition comprises, as an oxidation base, at least one compound of formula (I), and the addition salts thereof

wherein: a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R₁ may be identical or different, b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R₄ may be identical or different, c is equal to 0 or 1, R₁ is chosen from halogen atoms; C₁–C₈ aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO₂ group; and an onium radical Z; with the proviso that the radical R₁ does not comprise a peroxide bond or diazo, nitro or nitroso radicals, R₂ comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical, R₃ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyl radical; a hydroxyalkyl radical; an alkoxy radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an amino radical; a monoalkylamino radical; a dialkylamino; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical; R₄ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyalkyl radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical.
 38. The process according to claim 37, wherein the at least one oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes.
 39. The process according to claim 37, wherein the at least one oxidizing agent may be added to the dye composition at the time of application to the fibers or it may be applied in the form of an oxidizing composition simultaneously or sequentially with the application of the dye composition.
 40. A multi-compartment kit, wherein at least one first compartment comprises a dye composition comprising, as an oxidation base, at least one compound of formula (I), and the addition salts thereof

wherein: a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R₁ may be identical or different, b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R₄ may be identical or different, c is equal to 0 or 1, R₁ is chosen from halogen atoms; C₁–C₈ aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO₂ group; and an onium radical Z; with the proviso that the radical R₁ does not comprise a peroxide bond or diazo, nitro or nitroso radicals, R₂ comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical, R₃ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyl radical; a hydroxyalkyl radical; an alkoxy radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an amino radical; a monoalkylamino radical; a dialkylamino; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical; R₄ is chosen from an alkyl radical; an alkenyl radical; an alkynyl radical; a hydroxyalkyl radical; an alkoxyalkyl radical; an alkylcarbonyl radical; a hydroxyalkoxyalkyl radical; an aminoalkyl radical; an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals; a hydroxyl radical; a aminoalkyl radical; a carboxyl radical; a carboxyalkyl radical; a carbamoyl radical; a carbamoylalkyl radical; an alkoxycarbonyl radical; a monoalkylaminocarbonyl radical; a dialkylaminocarbonyl radical; a monoalkylaminocarbonylalkyl radical; and a dialkylaminocarbonylalkyl radical and at least one second compartment comprises at least one oxidizing agent. 